100 Best Americana & Country Songs of 2020 (Part 3: 50-26)

by Julian Spivey

50. "Welcome to Hard Times" by Charley Crockett
Charley Crockett likens the world amidst hard times to a rigged casino where you’re never going to break even (and oftentimes it feels like Hell) in “Welcome to Hard Times.” The title track from Crockett’s most recent album comes off like a pitch for sinning from the Devil himself, “do you like sinnin’?/well, you will before you go/we’ve got lots of gamblin’, ‘oh’ and we’re telling ties/you’re certainly welcome to hard times” all done with a old timey saloon like piano in the background. 

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49. "Skeletons" by Brothers Osborne
Some songs just come from one kick-ass creative phrase or hook and “Skeletons,” off Brothers Osborne’s 2020 release of the same name, is that with its take on having “skeletons in one’s closet” having “bones to pick with them.” The song written by the Osbornes (John and T.J.) with Adam and Andrew DeRoberts is everything that makes the duo the best currently in mainstream country music – a deep vocal from T.J., that killer lyric and some bad ass guitar playing from John. 

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48. "Working Man" by Tyller Gummersall
Songs of the working man have always been a part of the country music landscape because things have seemingly always been hard for the blue collar, working men and women of this country and one of the best “working man” songs of late is Tyller Gummersall’s “Working Man.” Gummersall sings about the hardships face by hard-working folks in this country, particularly the family farmer, and how it feels like “the patron saint of the working man” has finally retired. It’s essentially just Gummersall’s vocal and an acoustic guitar, but it’s one of the most powerful recordings of the year. 

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47. "Shut Up and Sing" by Brent Cobb
I absolutely hate the phrase “shut up and sing” from supposed music fans who don’t believe their favorite artists should partake in worldly views such as politics and how it’s their job to stick to their job of performing. I do, however, love the spin that Georgia singer-songwriter Brent Cobb put on the phrase this year with his track simply titled “Shut Up and Sing.” Cobb is going to sing, but he’s going to sing about whatever the hell he pleases – even if it includes topics like school shootings and poisonous political rhetoric – because it’s his job as a songwriter to be honest and sometimes that means telling it like it is. 

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46. "Ghosts" by Bruce Springsteen & the E Street Band
“Ghosts,” one of the most rocking tracks on Bruce Springsteen & the E Street Band’s latest album Letter to You, sees The Boss paying tribute to late bandmates from his pre-E Street Band days. When George Theiss, the singer of Springsteen’s first band The Castiles, died in 2018 it left Springsteen as the last living member of the band. It got him thinking of aging and the pain of losing friends and loved ones, which really is a theme of the new album. It’s not a sad song though as Springsteen belts in the chorus, “I’m alive and I can feel the blood shiver in my bones/I’m alive and I’m out here on my own/I’m alive, and I’m comin’ home.” Springsteen is very obviously going to rock until he can’t rock any longer and he’ll be carrying the ghosts of all of those who helped him get to where he is (the greatest songwriter in rock history, in my opinion) all the way. 

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45. "Under the Devil's Knee" by Tre Burt feat. Leyla McCalla, Allison Russell & Sunny War
I really wish this song hadn’t made this list this year because that means George Floyd and Breonna Taylor might still be alive and not more names on a growing list of unarmed black men and women killed by police brutality. But those things did happen and Tré Burt’s answer to those tragic events was potentially the most heart-wrenching and important protest song of 2020. Burt sings of the killings of Floyd, Taylor and Eric Garner (from 2014) and how life is just different for black people in this world when it comes to policing and those folks that don’t stand up in an effort to stop police brutality and complicit in it. The title and chorus refrain take its name from the fact that Minneapolis police officer Derek Chauvin killed Floyd by kneeling on his neck with his knee for more than nine minutes. Burt is joined by fellow black roots musicians Leyla McCalla, Sunny War and Allison Russell in the song’s devastating chorus. Proceeds from the song benefit the Community Justice Exchange’s National Bail Fund Network. 

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44. "Sunday Drive" by Brett Eldredge
One of the biggest country music shocks of 2020 for me was the seeming transformation of Brett Eldridge into a piano ballad singer-songwriter with some stuff that’s almost Randy Newman-esque on his latest release Sunday Drive. It’s the title track from that album that truly hits the listener in the feels with its tale of a family just going on a nice Sunday drive together and looking out upon the world and how those memories can truly stick with you (I know I have similar memories). Where the track truly gets your eyes, watering is when the narrator flips the script and ushers his elderly parents around on one of those Sunday drives and seeing as all those old memories flood back. 

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43. "Stone" by Ashley McBryde
It’s always fascinating when a songwriter can take a word or phrase and pull every ounce of meaning out of it and that’s exactly what Ashley McBryde does with “Stone” from her latest release Never Will. My first listens to “Stone” had me thinking it was likely about her father, but it turns out the inspiration was her late brother Clay, who committed suicide in 2018. The song explores the sadness and anger McBryde felt in coping with her brother’s death and how similar the two of them were. It’s an incredibly touching tune. 

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42. "I Called Mama" by Tim McGraw
Tim McGraw’s “I Called Mama,” written by Marv Green, Lance Miller and Jimmy Yeary, was particularly touching in 2020 when many of us have been unable to see loved ones like our mothers for much of the year. The song begins with its narrator getting a phone call from a friend about the passing of an old buddy and how his friend’s untimely death shook him up and gave him a bit more perspective on life. The narrator takes a bit of time just for himself to relax and watch nature and then, most importantly, make that phone call back home to his mama. “I Called Mama” is sure to bring a tear to your eye. 

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41. "Tuesday I'll Be Gone" by John Anderson & Blake Shelton
I was really excited to get some new music in 2020 from one of my favorite old chunks of coal in country music, John Anderson, and while the entirety of Years was a let down for me it did feature the fantastic “Tuesday I’ll Be Gone,” a duet with modern country music superstar Blake Shelton. Anderson sounds as good as ever on this track with his unique twang, which is fantastic to hear after he had dealt with some health issues in the years preceding the recording. The song, written by Anderson with his producers Dan Auerbach (of the rock duo The Black Keys) and David Ferguson, finds Anderson and Shelton swapping lines about the freedom of the road and of not really knowing what comes ahead of one in life. In addition to being happy to have another great Anderson song it’s also the best thing Shelton has put on a record in a few years. 

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40. "Shelby '65" by Kyle Nix
If you’re a fan of Red Dirt country music you probably already knew the name Kyle Nix, as he was (and hopefully one day will be again) the best damn fiddle player for the best damn band in Red Dirt – the Turnpike Troubadours. But in 2020 Nix showed that sawing on a hot fiddle wasn’t his only talent – he was also a very talented songwriter and could step out front and take on the role as frontman with his debut Lightning on the Mountain & Other Short Stories. My favorite track on the album is the rip-roaring “Shelby ‘65” that tells of two teenage lovers speeding through the night in a bit of American steel just daring the road to take them. “Shelby ‘65” is reminiscent to some of Turnpike Troubadours more raucous songs, like “Before the Devil Knows You’re Dead,” but it’s also proof Nix can be a Red Dirt superstar all on his own. 

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39. "Loved & Lost" by Porter Union
The married duo Porter Union (Cole Michael Porter and Kendra Porter) were contestants on the recent short-lived USA Network singing competition show “Real Country” and were selected to be on the show by ‘90s country hitmaker Travis Tritt who saw their potential. The duo released their sophomore album Loved & Lost independently in March and instantly the title track became one of the catchiest tunes of the year. The song, written by Porter Union with Jared Hicks and Oran Thornton, plays on the saying, “it’s better to have loved and lost than to never love at all” and adds the wonderful whoever said that “has never loved and lost someone like you.” It’s a throwback to something that might have dominated country radio back in Tritt’s day, which is probably what he saw in the duo. 

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38. "Damned Angel" by Hellbound Glory
I feel like Leroy Virgil, who makes music as Hellbound Glory, is the only artist who could get away with opening a song with the line: “Mama says you’ll be the death of me/you’re like methamphetamines” to a throwback to the sort of suave twang you’d hear under some smooth vocals by a Roy Orbison type. It’s a heartbreak ballad with Virgil’s raspy vocals filling in aptly where the smooth vocals of an Orbison or Chris Isaak may have been in its place. I’ve enjoyed Hellbound Glory’s rowdier side in the past, but it’s nice to see a bit of a scummy suavity to his music, as well. 

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37. "Love is Not Enough" by Lydia Loveless
There is a wry sense of humor in some of Lydia Loveless’s music and one of my favorite aspects of this is the line: “I can’t believe the worst kinds of people achieve everything they want/it takes medication to get me off.” In the song Loveless is calling out some of the cliches one might find in your typical love song or even relationship. Loveless told American Songwriter: “The song is a response to the old-fashioned idea that love is all you need, as opposed to understanding, or give and take. On a large scale, it’s about people who say things like, ‘love trumps hate’ and take zero action to make it true.”

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36. "I Remember Everything" by John Prine
The hardest musical moment of 2020 for me was the death of legendary singer-songwriter John Prine (essentially one of the fathers of the Americana genre) in early April from COVID-19 at age 73. Not only was it tragic because Prine was a legend and one of my favorites, but he was still at the top of his game as he’d shown on 2018’s The Tree of Forgiveness. It seems Prine was ready to give us another instant classic, but death took him too soon. In June, his final song “I Remember Everything” was release and is a lovely ballad about looking back on all the great things in one’s life – including one’s family and career. The song, which recently garnered two posthumous Grammy nominations for Prine, is just one more bit of proof of how he could take the little and simple things in life and bring so much poetry out of them. 

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35. "Me + Mine (Lamentations)" by American Aquarium
American Aquarium songwriter and frontman B.J. Barham has certainly proven himself as something as a songwriter for the working men and women of this country in his past AA albums, as well as his solo stuff. “Me + Mine (Lamentations)” certainly hits upon how this country treats the blue collar, hard-working folks among them with true to life lines like: “It’s like we don’t matter, mama said, at least that’s how it seems.” The song blasts politicians who promise to return jobs to these hard-working folks, knowing damn well they won’t be able to do so. Barham said on the American Aquarium website that he wrote down the word “lamentations” in 2018, knowing full well it’s what he wanted to name his next album. “Lamentations is one of the few books in the Bible where there’s this doubt of God. I saw a direct correlation between that and a Southern man today who voted for [President Donald] Trump. I wanted to write about a broken America and all the things that lead a human being to doubting something.” Nobody has written about a broken America better in these last few years than Barham. 

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34. "Smooth Shot of Whiskey" by Mike and the Moonpies & Mark Wystrach
Mike and the Moonpies, one of the most stellar and hardest working groups in the Texas Country/Red Dirt scene, released a unique tribute to the king of the honky tonks Gary Stewart this year with Touch of You – The Lost Songs of Gary Stewart. My favorite track on the album is “Smooth Shot of Whiskey,” penned by Stewart with songwriting legends Dean Dillon and Frank Dycus (whom you know well if you like classic George Strait). The song is a brotherly duet of sorts between close friends who’re both seeing relationships falter and want to drink about it over some smooth whiskey and Mike and the Moonpies singer Mike Harmeier is joined by Mark Wystrach of Midland in a perfect melding of voices. The tribute of Stewart songs that hadn’t yet reached the public was an important record for the band as Harmeier told Rolling Stone magazine: “The music of Gary Stewart has been the driving influence of our band from the first notes we played together.” 

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33. "Only Faster" by Chris Hennessee
Chris Hennessee’s “Only Faster” is the kind of unique spin on a love song I’m always looking for – likening his girl’s fast paced life to a racecar on the beaches of Daytona, a cannonball, a rocket launch and all sorts of other things and how she can break your heart even faster than all of those things. With a pulsating piano-driven backing, “Only Faster” is going to make you want to put your pedal to the floor if listening to it in the car. 

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32. "Space Force" by Western Centuries feat. Jim Lauderdale
I feel like “Space Force” by Western Centuries is intentionally cheeky because of how ridiculous the creation of a new military branch called the Space Force by the Trump Administration is, but maybe that’s just me putting my political spin on it. I looked it up – it’s most certainly intentionally cheeky with songwriter Jim Miller stating the real Space Force to be “one of the most ludicrous ideas ever to have been foisted upon the American taxpayer” in an interview with Seattle radio station KEXP. Even if it hadn’t been satirical, “Space Force” is a riotous blast talking about how fun it would be to be apart of the Space Force and chase all the bad guys around the galaxy. It’s essentially the band turning the Space Force into an old Western bounty hunter trip. The group is joined by singer-songwriter Jim Lauderdale on the track that never fails to put a smile on my face. 

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31. "Raining Horses" by Corb Lund
Agricultural Tragic just seems like a perfect title for a Corb Lund album and the Canadian country singer-songwriter tugs at the heartstrings with the catchy “Raining Horses” about a rancher who seemingly has too many horses, but doesn’t have the heart to give up on a beloved mare. According to Lund’s website: “The song is kind based around the idea of having too many horses on the place. But from a few steps back it’s more about desperation and eternal, irrational hope.” That “desperate and eternal, irrational hope” truly comes out within Lund’s vocal. 

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30. "The Curse" by Will Hoge
Will Hoge has proven he’s a many of many genres. He can write a straight up country ballad (check out “Even the River Runs Out of This Town” on this very list), he can write folky tunes, he can write rockers with a punk edge to them (check out “The Overthrow” on this very list), but maybe he’s at his best when playing the kind of heartland rock that artists like Bruce Springsteen, Tom Petty and John Mellencamp popularized. “The Curse,” off Hoge’s latest album Tiny Little Movies, is a tale about meeting the right person and how their love can have such a positive change on someone’s life, effectively turning it completely around. This one is sure to get stuck in your heads for days. 

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29. "Pawn Shop" by Brandy Clark
How many extremely important objects in a person’s life do you think have ended up in pawn shops because people needed quick cash to escape a life or change their life? Brandy Clark approaches this subject on her excellent “Pawn Shop,” co-written with Troy Vergas on her newest album Your Life is a Record. The third-person tale talks of a wedding ring given up after a dead relationship and a guitar given up by a musician who needs to change his career path to help feed his family. Clark told The Boot: “I was reading a book and a guy [working] at the pawn shop said, ‘I have the job of telling people that something’s not worth what they think it is.’ That really hit me as a song idea.” 

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28. "Letter to You" by Bruce Springsteen & the E Street Band
There’s a lot of dealing with mortality on Letter To You, the latest album from Bruce Springsteen and the E Street Band (the first as a band since 2012’s terrific Wrecking Ball), as “The Boss” and his bandmates are coming to terms with being senior citizens and knowing there’s less in front of them than there is behind. Despite their advanced age the band sounds better than ever as they recorded the album in just five days live in studio with no overdubs, just the raucous live energy they bring to their sometimes four hour live shows. The title track is one of the album’s highlights as it sees the aged rock star using his years and experience to pen a letter to someone (perhaps his younger self, perhaps his early bandmates with differing bands growing up who’re no long here or his faithful fan-base). 

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27. "Be Afraid" by Jason Isbell & the 400 Unit
The idea of musicians (and celebrities in general) using their platform to speak on topics such as politics and other important things rubs some people wrong. Jason Isbell thinks artists should do it anyway. “Be Afraid,” from Isbell and the 400 Unit’s latest release Reunions, is a call to action, in fact, for artists to try and inspire change – after all, most of the greats in the history of a multitude of musical genres have done just that. Isbell told Rolling Stone Country in February when the single came out: “If I don’t do what I considered to be the right thing – which is speak my mind – I’m not gonna be able to sleep when I’m an old man.” 

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26. "Starting Over" by Chris Stapleton
If there was ever a year to feel like just wiping the slate clean and starting over it would be 2020, maybe that’s why Chris Stapleton’s title track to his latest album Starting Over, his first single in over two years, just feels right. It could also be that Stapleton’s smooth, yet gruff soulful voice could probably sing the phone book and be pleasing to the ears and his harmonies with his wife Morgane are always incredible. “Starting Over,” co-written by Stapleton and his ex-SteelDrivers bandmate Mike Henderson, is essentially just he and his wife singing to an acoustic guitar and some light percussion. It may be simple, but it works flawlessly. 

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